Tuscany-Umbria Sojourn

Posted in Chianti, Tuscany and Umbria, Italy, Italy Popular Walks, Trips

Highlights of Tuscany-Umbria Sojourn

  • Stroll through the Renaissance town of Pienza.
  • Meander through the ancient streets and alleys of the medieval towns of Montalcino, Montepulciano and Cortona.
  • Experience lunch in a Tuscan farmhouse.
  • Sip a glass of world-class Brunello wine.
  • Walk in the hills around Montalcino and take in the sweeping vistas of the Val d’Orcia.
  • Visit the Umbrian towns of Orvieto and Todi.
  • Walk through the rolling Tuscan countryside.
  • Learn about the Etruscans.

Departure dates for Tuscany-Umbria Sojourn

Group Departures

May 5, 2016
September  4,  2016
October 10, 2016

Custom Departures are personalized to your schedule and are available on a year-round basis.

Choose your own personalized departure date-let us customize this trip to begin and end on a date that is convenient for you and your group.

Trip Length 6 days/5 nights
Start/Finish Florence/Orivieto
Walk Rating Moderate
Included All breakfasts, welcome lunch, most dinners
Hotels First Class/Luxury
Price $3,9250US
Single Supplement $775US



After a short drive from Florence, we begin a warm-up walk through the Renaissance town of Pienza and proceed to our welcome lunch in one of the old Monastaries overlooking the stunning Val d’Orcia. After lunch and our introductory talk, we will continue exploring the town of Pienza, birth place of 15th-century Pope Pius II, who commissioned the building of an ideal town based on Renaissance principles. Planned and built by architect Bernardo Rossellino in 1449, buildings are angled to show off the clear blue Tuscan skies. We then walk through some stunning landscape and into the surrounding countryside. Following our walk, we continue to Montalcino, famous for Brunello di Montalcino, one of Italy’s finest wines. There is time on your own before dinner to visit the ramparts of the town’s fortress for a magnificent view across the Val d’Orcia, wander the streets and shops of Montalcino or simply relax by the pool with a glass of limoncello. For dinner, we dine at a local restaurant in the medieval town of Montalcino.

The walk: 6 kms. /3.8 miles
Accommodations: Vecchia Oliviera, Montalcino, Relais Il Chiostro, Pienza, or similar property (L, D)

A restored olive mill, tastefully renovated with carefully chosen furnishings and carpets. Take in the sunset from the pool and gardens which overlook expansive vistas of the Val d’Orcia.


Our day begins with an Italian buffet breakfast. Our guides will take you to local specialty shops and grocers, where we will help you choose your own picnic lunch. Walking south from Montalcino through one of the best wine-producing zones in Italy, we meander through cool forests to the Abbey of Sant’Antimo – a 12th-century Romanesque structure fashioned in large part from luminous alabaster. Following our luncheon feast, we take a short walk to the nearby village of Castelnuovo dell’Abate. Before dinner, there is time for a tour of the small historical city of Montalcino and some leisure time. Before dinner we enjoy a tasting of exclusive Brunello wines. The evening meal is on your own at one of many charming local restaurant within easy walking distance from your hotel.

The walk: 4 kms./9 miles or 9 km. /5.5 miles
Accommodations: La Vecchia Oliviera, Montalcino, Reilais Il Chiostro, Pienza or similar property (B)


Today we walk through fertile valleys to the village of Monticchiello, set high on one of the many Tuscan hills. After lunch, we walk or transfer by car to Montepulciano, a miniature Florence famous for its Vino Nobile. We stop at Contucci, one of the oldest wineries in the region before transfering to our new accommodations just outside of Cortona. There is ample time to relax and freshen up before dinner, where the owners of the Relais Villa Baldelli will host us.

The walk: 14 kms. /9 miles; shorter options available
Accommodations: Relais Corte dei Papi or similar property (B, D)


Our morning begins with a walk around and into the old city of Cortona. Before lunch, take a tour of the museum to discuss the artist interpretations of Etruscan life. Enjoy lunch on your own, and time to wander around Cortona. Visit local shops and special spots that were used in the filming of “Under the Tuscan Sun.” We recommend a visit to the Cortona theatre. At 2:30 p.m., the group reconvenes and proceeds by private transport to the plain below Cortona where we visit large tumuli, or Etruscan family graves. Guests are welcome to participate in the entire excursion, or opt for the morning only. Dinner is on your own in the lovely town of Cortona.

The walk: 14 kms./9miles; shorter options available.
Accommodations: Relais Corte dei Papi or similar property (B)

The Relais Corte dei Papi offers luxury accommodations on the outskirts of Cortona. The family estate covers 190 hectares of gorgeous land.


We begin with an early transfer to Orvieto, a city that rises graciously above the bedrock. Following a guided walk of the city, you will have time on your own to enjoy lunch in a local restaurant. After lunch, you have the option of transferring to Todi, ranked among the most liveable city in the world or transfer directly to our accommodations for the evening. In Todi, we will explore some of the maze of Roman aqueducts and tunnels that run beneath the streets of Todi. Join us for drinks by the pool overlooking the dramatic landscape of Umbria followed by a farewell dinner.

The walk: 8 kms. /5 miles
Accommodations: Relais Todini or similar property (B, D)

Relais Todini, an elegantly restored 14th-century castle, is situated in the heart of 1300 hectares of private agricultural grounds. Enjoy panoramic vistas of the quiet and unpolluted Umbrian countryside from its hilltop position or take advantage of the spa facilities and pool.


Take an early morning walk around the private hills belonging to the Relais or enjoy a relaxing stroll through the gardens. Following breakfast, we say our good-byes and transfer train station, which offers easy access to Florence, Venice, the Cinque Terre, or Rome.

Accommodations: (B)

We are happy to book an extra night for you at the Relais Todini if you would like to take advantage of the spa and wellness center. (Additional charges apply).

NOT INCLUDED: Airfares, airport taxes, travel insurance (mandatory), pre and post trip arrangements, personal purchases, mini-bar services, alcohol unless specifically included.


B= breakfast included, L=lunch included, PicL=picnic lunch included, D=Dinner included
All bookings through Garth Allen Marksted Travel, Quebec Licensee.

* Choose your personalized Departure Date: We can customize any of our walking trips to begin on a date that is convenient to you. Supplemental charges may apply.

* Trips are offered in English.

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